A tandem hexaannulation reaction of benzyllithium involving base-induced cyclodehydrogenation

Hackfort T, Neumann B, Stammler H-G, Kuck D (1999)
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (11): 2879-2884.

Journal Article | Published | English

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Abstract
The reaction of the tribenzo[3.3.3]propellane ketone 1 (triptindan-9-one) with benzyllithium/TMEDA affords an efficient one-pot peri annulation of a dihydronaphthalene across two wings of the propellane framework. The key step of this surprising tandem reaction was determined to be a nucleophilic cyclization of (Z)-9-benzylidenetriptindane (4) with concomitant hydride elimination. The formation of the novel centrotetracyclo[5.5.5.6] framework bearing a distorted (E)-stilbene unit was confirmed by single-crystal X-ray structure analysis.
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Hackfort T, Neumann B, Stammler H-G, Kuck D. A tandem hexaannulation reaction of benzyllithium involving base-induced cyclodehydrogenation. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 1999;(11):2879-2884.
Hackfort, T., Neumann, B., Stammler, H. - G., & Kuck, D. (1999). A tandem hexaannulation reaction of benzyllithium involving base-induced cyclodehydrogenation. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(11), 2879-2884.
Hackfort, T., Neumann, B., Stammler, H. - G., and Kuck, D. (1999). A tandem hexaannulation reaction of benzyllithium involving base-induced cyclodehydrogenation. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2879-2884.
Hackfort, T., et al., 1999. A tandem hexaannulation reaction of benzyllithium involving base-induced cyclodehydrogenation. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (11), p 2879-2884.
T. Hackfort, et al., “A tandem hexaannulation reaction of benzyllithium involving base-induced cyclodehydrogenation”, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, pp. 2879-2884.
Hackfort, T., Neumann, B., Stammler, H.-G., Kuck, D.: A tandem hexaannulation reaction of benzyllithium involving base-induced cyclodehydrogenation. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2879-2884 (1999).
Hackfort, Thorsten, Neumann, Beate, Stammler, Hans-Georg, and Kuck, Dietmar. “A tandem hexaannulation reaction of benzyllithium involving base-induced cyclodehydrogenation”. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 11 (1999): 2879-2884.
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